1-Chloro-4-nitrobenzene → 1,1'-[(2,2-Dimethylpropane-1,3-diyl)bis(oxy)]bis(4-nitrobenzene)

HRID 2072854Notes

Reaction equation

HRID 2072854 reaction equation
[OH-:1].[Na+].[OH:3][CH2:4][C:5]([CH3:9])([CH2:7][OH:8])[CH3:6].[N+:10]([C:13]1[CH:18]=[CH:17][C:16](Cl)=[CH:15][CH:14]=1)([O-:12])=[O:11]>CS(C)=O>[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([O:3][CH2:4][C:5]([CH3:9])([CH3:6])[CH2:7][O:8][C:16]2[CH:17]=[CH:18][C:13]([N+:10]([O-:11])=[O:1])=[CH:14][CH:15]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 31344Neopentyl glycol

Product 1

HCID 141211811,1'-[(2,2-Dimethylpropane-1,3-diyl)bis(oxy)]bis(4-nitrobenzene)

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

140 g powdered sodium hydroxide were added in small portions with thorough stirring over a period of 3 hours to a solution of 104 g (1 mol) neopentyl glycol and 346.5 g (2.2 mols) 4-nitrochlorobenzene in 600 ml dimethylsulfoxide (DMSO). An internal temperature of 40°-50° C. was maintained by cooling with ice both during the addition and subsequently until the exothermic reaction abated. The reaction mixture was then stirred for 8 hours at 25° C. The product precipitated was filtered off under suction, washed first with water until neutral and then once with ethyl acetate and then dried in vacuo at 90° C.

Workup

  1. temperatureAn internal temperature of 40°-50° C. was maintained
  2. temperatureby cooling with ice both
  3. additionduring the addition
  4. customsubsequently until the exothermic reaction
  5. customThe product precipitated
  6. filtrationwas filtered off under suction
  7. washwashed first with water until neutral and then once with ethyl acetate
  8. customdried in vacuo at 90° C.

Sources & evidence

ORD record
ord-b258365fb6564aab83be945054c39264
Source dataset
uspto-grants-1990_04
Patent number
US04914238

Reaction notes

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